Freitag has served as principal investigator for a number of research projects including several large, multi-institutional efforts. His research goals have focused on the automation of data science; the automatic extension of mechanistic models through machine reading; knowledge federation over diverse information sources through data analytics and natural language processing; explaining the spread of ideas through online communities; and novel approaches to institutional knowledge management using controlled English.

Before joining SRI in 2009, Freitag led and participated in fundamental research at Fair Isaac Corporation with a special focus on the rapid deployment of textual information extraction, and the unsupervised induction of linguistic structure and function through corpus analysis. He also was a research scientist and vice president for technology at Burning Glass Technologies, LLC, which develops solutions for human resource management using machine learning and natural language processing. Between 1998 and 2000, Freitag conducted information extraction and information retrieval research at Just Research.

Freitag holds a B.A. in English literature from Reed College, and a Ph.D. in computer science from Carnegie Mellon University.